Chicago would be receiving a pick for freeing up 5 million. We can spend that cap way better in free agency otherwise.

Lindholm already lost tens of millions from not signing his contract offer last year in Calgary. He's not taking another gamble on himself. Another bad season like this year again and he might never get a multi-year offer.

no they won't plenty of other teams will take Smith.

Maybe if the Pens retained on him, most teams will probably look to spend 5 AAV better than on Smith.

except the FA market sucks, so really instead of getting roped into term, they will take smith on a 1 year deal with no retention for a draft pick that has minimal chance of ever generating an actual NHL player.

I can’t comment on all other 30 teams, but Chicago won’t pay for Smith.

A. that's not really true and B. the only reason you have is that you are in a rebuild but that's not really a reason.
If they find they can buy for a 3rd or 4th, and flip for a 2nd or 3rd.... CHI would make that move, as it's an expiring deal.

That's why rebuilding teams love expiring contracts. They can pump and dump them.

But there are other teams that would pay for Smith, because the market sucks. Every team that loses a guy has to replace a guy. There just aren't enough to go around.
So someone would take a run at it.
The only reason he wasn't moved last year is people didn't want to carry into FA. But that isn't a problem going forward next year. So after the FA market settles and people are looking for a forward, that's when he'll get moved. As there are teams out there that are going to want better than what they currently have, and may find getting an expiring deal is a better idea than signing a contract with term on what is available.

Chicago’s exit interviews had a common theme among players; too many guys are playing for themselves and not the team. So, getting a player with the intention of flipping them at the deadline is not likely to motivate Chicago to make a deal.

when teams have A. cap space, B. roster space, and C. a need to improve, these are the things that happen.
Every guy in a contract year is playing for themselves. You would too if it was your money.
The reality is if CHI thinks it can turn Smith to a 30 goal scorer and flip him for a 2nd + they would make that move.
Maybe they don't think and think it's more likely he'll be a roughly 20 goal 40 point guy. At which point what they would be willing to pay vs what they would be willing to give up will differ.
You are right that a team might think, the 3rd or 4th round pick we might get on guy X might not be worth the trouble of bringing in guy X.
It all varies on the level of return they think a guy can bring. They might think it's worth bringing him in, wait for injury to strike a team, and retain and ship off for that pick.
It really just depends on the believed value of a player.